The present invention relates to a novel process. In particular, the present invention relates to a new process for forming 2-substituted alkyl (2-substituted alkyl)carbamates in high yield and selectivity.
The 2-haloalkyl (2-haloalkyl)carbamates have useful fungicidal and bactericidal properties. For example, it is known that treatment with 500 ppm of (2-chloroethyl)methyl-2-chloroethyl ester completely inhibited growth of the following: Lactobacillus casei, Erwinia amylovora, Fuso bact necrophorum 10, Piricularia oryzac, Aspergillus niger, Mucor miehei atcc 16457, Staphylococcus aureus atcc, Actinomyces viscosis, Clostridium perfringens, Clostridium septicum, Bacteroides fragilis, Bacteroides multiacidus, Streptococcus faecalis, Streptococcus bovis, Bacillus subtilis, Streptococcus mutans and Candida albicans nih. Additionally, (2-chloroethyl)-(2-methoxylmethyl)-2-chloroethyl ester selectively completely inhibited symptoms of tobacco black shank when infected soil was planted after the soil was drenched in 25 ppm water solution of (2-chloroethyl)-(2-methoxymethyl)-2-chloroethyl ester.
It has been previously known to prepare 2-haloalkyl-N-(2-haloalkyl)carbamates by addition of 2-haloalkylamines to 2-haloalkyl haloformates. The following schematic representation illustrates this process. ##STR1## By substituting an alkyl trichloroacetate for the haloformate, the by-product is chloroform instead of hydrogen chloride, e.g., ##STR2##
A second process disclosed by Dorschner et al., U.S. Pat. No. 3,885,954, employs the reaction of an isocyanate with an alcohol according to the following scheme: ##STR3##
Additionally, it has been disclosed by H. Driguez et al., Can. J. Chem., 55(4), 700-1 (1977), that N-halocarbamates will react with olefins under appropriate conditions to add nitrogen to the least substituted reactive position of the olefin, e.g., ##STR4##
Previously known processes have employed starting materials that are expensive, unstable over long time periods or otherwise handled only with difficulty. In addition, the process of Dorschner et al. is limited to preparation of mono-N-substituted carbamates only.
It would be desirable to prepare 2-haloalkyl-N-(2-haloalkyl)carbamates in high yields and selectivity employing readily available and chemically stable oxazolidinones.